US4083685A - Process for dyeing synthetic fibre materials from an organic water-immiscible solvent - Google Patents
Process for dyeing synthetic fibre materials from an organic water-immiscible solvent Download PDFInfo
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- US4083685A US4083685A US05/703,013 US70301376A US4083685A US 4083685 A US4083685 A US 4083685A US 70301376 A US70301376 A US 70301376A US 4083685 A US4083685 A US 4083685A
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Classifications
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
- D06P1/908—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof using specified dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
- D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
- D06P1/922—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons
- D06P1/924—Halogenated hydrocarbons
Definitions
- the invention relates to an exhaustion process for dyeing synthetic fibre materials, which is characterised in that dispersions of azo dyestuffs which contain at least one grouping of the formula ##STR1## wherein
- X denotes a direct bond or a bridge member
- A denotes an alkylene radical
- R 1 denotes hydrogen or alkyl
- R 2 denotes hydrogen, alkyl, cycloalkyl, aralkyl, OH,
- An optionally substituted amino group or aryl are used in organic water-immiscible solvents.
- Suitable azo dyestuffs for this purpose are those of which the diazo component can belong either to the aromatic-carbocyclic or to the aromatic-heterocyclic series, and of which the coupling component is a benzene compound or heterocyclic compound customary in azo dyestuff chemistry.
- the radical of the formula I which characterises the dyestuffs to be used can be present 1 to 3 times in the basic molecule.
- bridge members X are, for example, the following: --NY--, --O--, --S--, --CO--, --CONY--, --SO 2 -- and --SO 2 NY wherein
- Y denotes hydrogen, optionally substituted alkyl or the radical ##STR2##
- Suitable alkylene radicals A are straight-chain or branched C 1 -C 4 -alkylene radicals which can be interrupted by hetero-atoms, such as O and S, and can be substituted by nonionic substituents, such as OH, Halogen or ##STR3##
- Suitable alkyl radicals R 1 , R 2 and Y are those with 1 to 6 C atoms which are saturated or unsaturated and can be substituted, preferably monosubstituted by OH, halogen, CN, C 1 -C 4 -alkoxy or C 2 -C 5 -alkoxycarbonyl.
- Suitable cycloalkyl radicals R 2 are cyclohexyl radicals which can optionally be substituted by methyl or chlorine.
- Suitable aralkyl radicals R 2 are benzyl and phenylethyl radicals.
- Suitable amino groups R 2 are those of the formula --NR 3 R 4 wherein
- R 3 and R 4 denote hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -hydroxyalkyl and
- R 4 also denotes phenyl or tolyl.
- Suitable aryl radicals R 2 are phenyl radicals which are optionally substituted by OH, C 1 -C 4 -alkyl, halogen or C 1 -C 4 -alkoxy.
- halogen there is preferably to be understood, within the scope of this invention, F, Br and above all Cl.
- Azo dyestuffs to be used preferentially correspond to the formula ##STR4## wherein
- D denotes the radical of an aromatic-carbocyclic or aromatic-heterocyclic diazo component
- Q 1 denotes hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen, alkylcarbonylamino which is optionally monosubstituted by OH, halogen, CN or C 1 -C 4 -alkoxy, phenylcarbonylamino which is optionally monosubstituted to trisubstituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or OH, formylamino or ureido,
- Q 2 denotes hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen
- Q 3 denotes hydrogen, C 1 -C 4 -alkyl which is optionally substituted by CN, Cl, CONH 2 or C 1 -C 2 -alkoxy, or denotes -C 2 H 4 OCONHQ 4 ,
- Q 4 denotes hydrogen, amino, C 1 -C 4 -alkylamino, C 1 -C 4 -hydroxyalkylamino, OH, methyl or hydroxyphenyl and
- A' denotes C 1 -C 4 -alkylene, preferably -C 2 H 4 --.
- Q 2 preferably represents H.
- the radical D preferably represents a benzene or thiadiazole radical which is optionally substituted by non-ionic radicals, non-ionic radicals being understood both as the group ##STR5## and as other radicals customary in dyestuff chemistry, such as Cl, Br, CN, NO 2 , C 1 -C 4 -alkyl, CONH 2 , SO 2 NH 2 and C 1 -C 4 -alkylsulphonyl.
- Dyestuffs which are very particularly suitable for the dyeing process according to the invention are those of the formula II, wherein
- T 1 denotes H, NO 2 , CN, halogen or CONH 2 ,
- T 2 denotes H, NO 2 , CN, CONH 2 or SO 2 NH 2 .
- T 3 denotes H, NO 2 , CN, halogen or C 1 -C 4 -alkylsulphonyl and
- T 4 denotes H or halogen.
- Ar denotes a benzene-type diazo component which is free of ionic groups
- B denotes a heterocyclic coupling component of the pyrazolone, aminopyrazole, indole or imidazole series and
- Y 1 and Y 2 denote hydrogen or the --X--A--OCONR 1 R 2 radical, but do not simultaneously denote hydrogen.
- the dyestuffs to be used according to the invention are largely known or easily obtainable according to known processes (U.S. Pat. No. 2,238,486, German Patent Specification No. 1,061,927, French Patent Specification Nos. 1,594,835, 1,360,450 and 2,079,167, German Offenlegungsschriften (German Published Specifications) No. 1,644,126 and 2,145,412, Japanese Patent Publication No. 3009/67 and British patent specification No. 1,237,017).
- Organic water-immiscible solvents which can be used are those of boiling point between 60° and 170° C, for example aliphatic chlorohydrocarbons or aliphatic fluorohydrocarbons and fluorochlorohydrocarbons, as well as aromatic chlorohydrocarbons and fluorohydrocarbons.
- Tetrachloroethylene, trichloroethylene, 1,1,1-trichloroethane and 1,1,1-trichloropropane have proved particularly suitable. Mixtures of these solvents can also be used.
- the dyeing liquors can contain up to 3 percent by weight of water, based on the weight of the organic solvents.
- Non-ionic auxiliaries which can be used are in particular the known surface-active ethoxylation and propoxylation products of fatty alcohols, alkylphenols, fatty acid amides and fatty acids as well as their mixtures; the auxiliaries are employed in an amount of 0.05-2 percent by weight, based on the weight of the organic solvents.
- they can also be used with advantage for pasting the dyestuffs containing carbamate groups, and can in this way be added to the dyeing liquors in the form of a dyestuff/auxiliary paste.
- the synthetic fibre materials to be dyed according to the invention are above all fibre materials of aromatic polyesters, cellulose esters, polyacrylonitrile, synthetic polyamides and polyurethanes.
- the fibre materials can be in the most diverse stages of processing, for example in the form of filaments, flocks, tops, yarn, piece goods, such as woven fabric or knitted fabric, or made-up goods.
- the dyeing according to the invention is preferably carried out in closed apparatuses, at temperatures of 60° to 170° C.
- the dyeing times lie between 5 and 90 minutes.
- the dyestuffs, containing carbamate groups, to be used according to the invention are largely insoluble in the organic water-immiscible solvents. They are distinguished by good affinity and good general fastness properties.
- a further subject of the present invention are new azo dyestuffs of the formulae ##STR7## wherein
- V 1 denotes NO 2 , CN, C 1 -C 4 -alkylsulphonyl, Cl, Br or H,
- V 2 denotes H, chlorine, methyl, methoxy or ethoxy
- V 3 denotes H, methoxy or ethoxy
- V 4 denotes C 1 -C 4 -alkyl, cyanoethyl or -V 5 -OCONHV 6 ,
- V 5 denotes C 1 -C 4 -alkylene
- V 6 denotes H or C 1 -C 4 -hydroxyalkyl
- V 7 represents carbamoyl or sulphamoyl
- V 2 -V 5 have the abovementioned meaning
- V 6 represents H, methyl, ethyl, hydroxyethyl, phenyl, tolyl or hydroxyphenyl; ##STR9## wherein
- V 1 , V 3 , V 4 and V 5 have the abovementioned meaning
- V 2 represents formylamino, C 2 -C 5 -alkylcarbonylamino
- V 6 represents H, methyl, ethyl or hydroxyethyl; and also ##STR10## wherein
- V 1 ' represents CN
- W 1 represents H, Cl, Br, CN, CF 3 , CH 3 , OCH 3 or CONH 2 ,
- W 2 represents H, Cl, Br, CN, CF 3 or CH 3 ,
- W 3 represents H or CH 3 .
- V 2 represents H, Cl, CH 3 , OCH 3 , OC 2 H 5 , NHCHO, C 2 -C 5 -alkylcarbonylamino, H 2 NCONH or benzoylamino,
- V 3 represents H, CH 3 , OCH 3 or OC 2 H 5 ,
- V 4 represents C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl radicals which are optionally substituted by 1 or 2 nitrile groups, or represents -V 5 -OCONHV 6 ,
- V 5 represents C 2 -C 4 -alkylene which is optionally substituted by a further OCONHV 6 group and
- V 6 represents H, OH, C 1 -C 4 -hydroxyalkyl or C 3 -C 4 -dihydroxyalkyl.
- V 1 represents Cl, Br, NO 2 or CN
- V 5 represents -C 2 H 4 -
- V 4 represents cyanoethyl or -V 5 OCONHV 6 and the remaining radicals have the abovementioned meaning
- V 1 , V 3 and V 6 represent H, V 2 represents H or CH 3 ,
- V 4 represents cyanoethyl or V 5 -OCONHV 6 and
- V 5 represents -C 2 H 4 -;
- V 4 represents cyanoethyl or -V 5 -OCONHV 6 ,
- V 6 represents H and the remaining radicals have the abovementioned meaning
- V 2 represents acetylamino
- V 4 represents cyanoethyl or -V 5 -OCONHV 6 ,
- V 5 represents -C 2 H 4 -
- V 6 represents hydrogen and the remaining radicals have the abovementioned meaning
- V 1 ' is the o- or p-position to the azo bridge
- W 1 denotes Cl or CN
- W 2 denotes H, Cl or CH 3 ,
- W 3 denotes H or CH 3 .
- V 2 denotes H, CH 3 , formylamino, NHCONH 2 or acetylamino, preferably H,
- V 3 denotes H, OCH 3 or OC 2 H 5 ,
- V 4 denotes C 2 H 5 , C 2 H 4 CN, C 2 H 4 OC 2 H 4 CN or CH 2 CHCNCH 2 CN, preferably C 2 H 4 CN,
- V 5 denotes --C 2 H 4 --
- V 6 denotes H or C 2 H 4 OH.
- the new dyestuffs are obtained according to methods which are in themselves known, for example by diazotising corresponding anilines and coupling with corresponding coupling components.
- Suitable diazo components are: 2-cyano-4-nitroaniline, 2,4-dicyanoaniline, 2,5-dicyanoaniline, 2,4-dicyano-6-chloroaniline, 2,4-dicyano-3,5-dimethylaniline, 2,5-dichloro-4-cyanoaniline, 2,4-dinitro-6-bromoaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-cyano-aniline, 2,6-dicyano-4-nitro-aniline, 2-cyano-4-nitro-6-methylsulphonylaniline, 2-cyano-4-nitro-6-chloro-aniline, 2-cyano-4-nitro-6-bromo-aniline, 4-carbamoylaniline and 4-sulphamoylaniline.
- Suitable coupling components are: ##STR11##
- the new dyestuffs can, however, also be obtained by, for example, reacting azo dyestuffs containing the grouping
- Q denotes chlorine or bromine and in the case that Z denotes phenoxycarbonyl, reacting with amines of the formula NHR 1 R 2 in a manner which is in itself known (compare, for example, GB Pat. No. 1,241,705).
- Those dyestuffs which contain nitrile groups in the 2,6-position of the diazo component are advantageously obtained by reaction of corresponding 2,6-dihalogenoazo dyestuffs with CuCN or CuCN-forming substances in aprotic polar organic solvents at temperatures of about 60°-120° C in a known manner (compare GB-PS No. 1,125,683).
- the new dyestuffs are particularly suitable for dyeing the abovementioned types of fibres from organic solvents by the exhaustion process, and for the continuous dyeing of, preferably, polyester fibres with aqueous and non-aqueous padding liquors.
- a polyethylene terephthalate fibre fabric 100 parts of a polyethylene terephthalate fibre fabric are introduced into a dyebath which has been prepared from 1 part of the dyestuff of the formula ##STR13## which has been brought to a finely divided state by grinding, and 1,000 parts of tetrachloroethylene.
- the bath is brought to 120° C, with vigorous agitation of the liquor, and is kept at this temperature for 30 minutes. After brief cooling, the liquor is separated off and the dyed goods are rinsed three times with fresh perchloroethylene at 60° C. After drying, a strong intense red dyeing of high colour yield and very good fastness to light and to washing is obtained.
- a triacetate yarn 100 parts of a triacetate yarn are introduced into a dyebath which consists of 1 part of finely ground dyestuff of the formula ##STR14## and 1,000 parts of tetrachloroethylene.
- the dyebath is brought to 100° C with vigorous agitation of the liquor and is kept at this temperature for 30 minutes. After cooling, and rinsing the dyed goods with fresh tetrachloroethylene, a very strong red dyeing of good fastness to light and to washing is obtained.
- 100 parts of texturised polyethylene terephthalate fibres are introduced into a dyebath which has been prepared from 1 part of finely ground dyestuff of the formula ##STR15## 1,000 parts of tetrachloroethylene, 1 part of oleic acid ethanolamide, 1 part of oleyl alcohol eicosa-ethylene glycol ether and 6 parts of water.
- the system is warmed to 120° C in a closed apparatus, with vigorous agitation of the liquor, and the fibres are dyed at this temperature for 30 minutes. After cooling to approx. 80° C and rinsing with fresh tetrachloroethylene at 60° C, a strong green dyeing of good colour yield and good fastness to light and washing is obtained.
- the bath is brought to 100° C with vigorous agitation of the liquor and is kept at this temperature for 30 minutes. After separating off the dyeing liquor and twice rinsing with fresh tetrachloroethylene, a very deep and fast yellow dyeing is obtained.
- a polyethylene terephthalate fibre fabric 100 parts of a polyethylene terephthalate fibre fabric are introduced into a dyebath which has been prepared from 1 part of the dyestuff of the formula ##STR117## which has been brought to a finely divided state by grinding, and 1,000 parts of tetrachloroethylene.
- the bath is brought to 120° C whilst vigorously agitating the liquor and is kept at this temperature for 30 minutes. After brief cooling, the liquor is separated off and the dyed goods are rinsed three times with fresh perchloroethylene at 60° C. After drying, a strong intense scarlet dyeing of high colour yield and very good fastness to light and to washing is obtained.
- a triacetate yarn 100 parts are introduced into a dyebath which consists of 1 part of finely ground dyestuff of the formula ##STR118## and 1,000 parts of tetrachloroethylene.
- the dyebath is brought to 100° C with vigorous agitation of the liquor and is kept at this temperature for 30 minutes. After cooling, and rinsing the dyed goods with fresh tetrachoroethylene, a very strong orange dyeing with good fastness to light and to washing is obtained.
- 100 parts of texturised polyethylene terephthalate fibres are introduced into a dyebath which has been prepared from 1 part of finely ground dyestuff of the formula ##STR119## 1,000 parts of tetrachloroethylene, 1 part of oleic acid ethanolamide, 1 part of oleyl alcohol eicosa-ethylene glycol ether and 6 parts of water.
- the system is warmed to 120° C in a closed apparatus with vigorous agitation of the liquor, and the fibres are dyed at this temperature for 30 minutes. After cooling to approx. 80° C, and rinsing with fresh tetrachloroethylene at 60° C, a strong red dyeing of good colour yield and good fastness to light and to washing is obtained.
- a scarlet dyeing of excellent rub resistance is obtained, with a high fixing yield.
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Abstract
Exhaustion process for dyeing synthetic fiber materials with dispersions of azo dyestuffs which contain carbamate groups, in organic water-immiscible solvents. The dyestuffs are distinguished by good drawing properties and good general fastness properties.
Description
This is a continuation, of application, Ser. No. 474,990, filed May 31, 1974, now abandoned.
The invention relates to an exhaustion process for dyeing synthetic fibre materials, which is characterised in that dispersions of azo dyestuffs which contain at least one grouping of the formula ##STR1## wherein
X denotes a direct bond or a bridge member,
A denotes an alkylene radical,
R1 denotes hydrogen or alkyl and
R2 denotes hydrogen, alkyl, cycloalkyl, aralkyl, OH,
An optionally substituted amino group or aryl are used in organic water-immiscible solvents.
Suitable azo dyestuffs for this purpose are those of which the diazo component can belong either to the aromatic-carbocyclic or to the aromatic-heterocyclic series, and of which the coupling component is a benzene compound or heterocyclic compound customary in azo dyestuff chemistry.
The radical of the formula I which characterises the dyestuffs to be used can be present 1 to 3 times in the basic molecule.
Preferred radicals I are those with R1 and R2 = hydrogen.
The bridge members X are, for example, the following: --NY--, --O--, --S--, --CO--, --CONY--, --SO2 -- and --SO2 NY wherein
Y denotes hydrogen, optionally substituted alkyl or the radical ##STR2##
Suitable alkylene radicals A are straight-chain or branched C1 -C4 -alkylene radicals which can be interrupted by hetero-atoms, such as O and S, and can be substituted by nonionic substituents, such as OH, Halogen or ##STR3##
Suitable alkyl radicals R1, R2 and Y are those with 1 to 6 C atoms which are saturated or unsaturated and can be substituted, preferably monosubstituted by OH, halogen, CN, C1 -C4 -alkoxy or C2 -C5 -alkoxycarbonyl.
Suitable cycloalkyl radicals R2 are cyclohexyl radicals which can optionally be substituted by methyl or chlorine.
Suitable aralkyl radicals R2 are benzyl and phenylethyl radicals.
Suitable amino groups R2 are those of the formula --NR3 R4 wherein
R3 and R4 denote hydrogen, C1 -C4 -alkyl or C1 -C4 -hydroxyalkyl and
R4 also denotes phenyl or tolyl.
Suitable aryl radicals R2 are phenyl radicals which are optionally substituted by OH, C1 -C4 -alkyl, halogen or C1 -C4 -alkoxy.
By halogen there is preferably to be understood, within the scope of this invention, F, Br and above all Cl.
Azo dyestuffs to be used preferentially correspond to the formula ##STR4## wherein
D denotes the radical of an aromatic-carbocyclic or aromatic-heterocyclic diazo component,
Q1 denotes hydrogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, halogen, alkylcarbonylamino which is optionally monosubstituted by OH, halogen, CN or C1 -C4 -alkoxy, phenylcarbonylamino which is optionally monosubstituted to trisubstituted by C1 -C4 -alkyl, C1 -C4 -alkoxy, halogen or OH, formylamino or ureido,
Q2 denotes hydrogen, C1 -C4 -alkyl, C1 -C4 -alkoxy or halogen,
Q3 denotes hydrogen, C1 -C4 -alkyl which is optionally substituted by CN, Cl, CONH2 or C1 -C2 -alkoxy, or denotes -C2 H4 OCONHQ4,
Q4 denotes hydrogen, amino, C1 -C4 -alkylamino, C1 -C4 -hydroxyalkylamino, OH, methyl or hydroxyphenyl and
A' denotes C1 -C4 -alkylene, preferably -C2 H4 --.
Q2 preferably represents H.
The radical D preferably represents a benzene or thiadiazole radical which is optionally substituted by non-ionic radicals, non-ionic radicals being understood both as the group ##STR5## and as other radicals customary in dyestuff chemistry, such as Cl, Br, CN, NO2, C1 -C4 -alkyl, CONH2, SO2 NH2 and C1 -C4 -alkylsulphonyl.
Dyestuffs which are very particularly suitable for the dyeing process according to the invention are those of the formula II, wherein
D represents the radical ##STR6## wherein
T1 denotes H, NO2, CN, halogen or CONH2,
T2 denotes H, NO2, CN, CONH2 or SO2 NH2.
T3 denotes H, NO2, CN, halogen or C1 -C4 -alkylsulphonyl and
T4 denotes H or halogen.
Further dyestuffs to be used preferentially correspond to the formula
Y.sub.1 --Ar--N═N--B--Y.sub.2 (III)
wherein
Ar denotes a benzene-type diazo component which is free of ionic groups,
B denotes a heterocyclic coupling component of the pyrazolone, aminopyrazole, indole or imidazole series and
Y1 and Y2 denote hydrogen or the --X--A--OCONR1 R2 radical, but do not simultaneously denote hydrogen. The dyestuffs to be used according to the invention are largely known or easily obtainable according to known processes (U.S. Pat. No. 2,238,486, German Patent Specification No. 1,061,927, French Patent Specification Nos. 1,594,835, 1,360,450 and 2,079,167, German Offenlegungsschriften (German Published Specifications) No. 1,644,126 and 2,145,412, Japanese Patent Publication No. 3009/67 and British patent specification No. 1,237,017).
The dyeing of synthetic fibre materials from organic solvents by the so-called exhaustion process is generally known. Organic water-immiscible solvents which can be used are those of boiling point between 60° and 170° C, for example aliphatic chlorohydrocarbons or aliphatic fluorohydrocarbons and fluorochlorohydrocarbons, as well as aromatic chlorohydrocarbons and fluorohydrocarbons.
Tetrachloroethylene, trichloroethylene, 1,1,1-trichloroethane and 1,1,1-trichloropropane have proved particularly suitable. Mixtures of these solvents can also be used.
The dyeing liquors can contain up to 3 percent by weight of water, based on the weight of the organic solvents.
Furthermore, an addition of non-ionic auxiliaries to the dyeing liquors has proved of value in some cases. Non-ionic auxiliaries which can be used are in particular the known surface-active ethoxylation and propoxylation products of fatty alcohols, alkylphenols, fatty acid amides and fatty acids as well as their mixtures; the auxiliaries are employed in an amount of 0.05-2 percent by weight, based on the weight of the organic solvents. Instead of adding the auxiliaries directly to the dyeing liquors, they can also be used with advantage for pasting the dyestuffs containing carbamate groups, and can in this way be added to the dyeing liquors in the form of a dyestuff/auxiliary paste.
The synthetic fibre materials to be dyed according to the invention are above all fibre materials of aromatic polyesters, cellulose esters, polyacrylonitrile, synthetic polyamides and polyurethanes. The fibre materials can be in the most diverse stages of processing, for example in the form of filaments, flocks, tops, yarn, piece goods, such as woven fabric or knitted fabric, or made-up goods.
The dyeing according to the invention is preferably carried out in closed apparatuses, at temperatures of 60° to 170° C. The dyeing times lie between 5 and 90 minutes.
The dyestuffs, containing carbamate groups, to be used according to the invention are largely insoluble in the organic water-immiscible solvents. They are distinguished by good affinity and good general fastness properties.
A further subject of the present invention are new azo dyestuffs of the formulae ##STR7## wherein
V1 denotes NO2, CN, C1 -C4 -alkylsulphonyl, Cl, Br or H,
V2 denotes H, chlorine, methyl, methoxy or ethoxy,
V3 denotes H, methoxy or ethoxy,
V4 denotes C1 -C4 -alkyl, cyanoethyl or -V5 -OCONHV6,
V5 denotes C1 -C4 -alkylene and
V6 denotes H or C1 -C4 -hydroxyalkyl; ##STR8## wherein
V7 represents carbamoyl or sulphamoyl and
V2 -V5 have the abovementioned meaning and
V6 represents H, methyl, ethyl, hydroxyethyl, phenyl, tolyl or hydroxyphenyl; ##STR9## wherein
V1, V3, V4 and V5 have the abovementioned meaning,
V2 represents formylamino, C2 -C5 -alkylcarbonylamino,
H2 NCONH- or benzoylamino and
V6 represents H, methyl, ethyl or hydroxyethyl; and also ##STR10## wherein
V1 ' represents CN,
W1 represents H, Cl, Br, CN, CF3, CH3, OCH3 or CONH2,
W2 represents H, Cl, Br, CN, CF3 or CH3,
W3 represents H or CH3,
V2 represents H, Cl, CH3, OCH3, OC2 H5, NHCHO, C2 -C5 -alkylcarbonylamino, H2 NCONH or benzoylamino,
V3 represents H, CH3, OCH3 or OC2 H5,
V4 represents C1 -C4 -alkyl or C1 -C4 -alkoxy-C2 -C4 -alkyl radicals which are optionally substituted by 1 or 2 nitrile groups, or represents -V5 -OCONHV6,
V5 represents C2 -C4 -alkylene which is optionally substituted by a further OCONHV6 group and
V6 represents H, OH, C1 -C4 -hydroxyalkyl or C3 -C4 -dihydroxyalkyl.
Very particularly preferred new dyestuffs are
(a1) those of the formula IV, wherein
V1 represents Cl, Br, NO2 or CN,
V5 represents -C2 H4 - and
V4 represents cyanoethyl or -V5 OCONHV6 and the remaining radicals have the abovementioned meaning;
(a2) and also those of the formula IV, wherein
V1, V3 and V6 represent H, V2 represents H or CH3,
V4 represents cyanoethyl or V5 -OCONHV6 and
V5 represents -C2 H4 -;
(b) those of the formula V, wherein
V4 represents cyanoethyl or -V5 -OCONHV6,
V6 represents H and the remaining radicals have the abovementioned meaning;
(c) those of the formula VI, wherein
V2 represents acetylamino,
V4 represents cyanoethyl or -V5 -OCONHV6,
V5 represents -C2 H4 - and
V6 represents hydrogen and the remaining radicals have the abovementioned meaning; and
(d) those of the formula VII, wherein
V1 ' is the o- or p-position to the azo bridge,
W1 denotes Cl or CN,
W2 denotes H, Cl or CH3,
W3 denotes H or CH3,
V2 denotes H, CH3, formylamino, NHCONH2 or acetylamino, preferably H,
V3 denotes H, OCH3 or OC2 H5,
V4 denotes C2 H5, C2 H4 CN, C2 H4 OC2 H4 CN or CH2 CHCNCH2 CN, preferably C2 H4 CN,
V5 denotes --C2 H4 -- and
V6 denotes H or C2 H4 OH.
The new dyestuffs are obtained according to methods which are in themselves known, for example by diazotising corresponding anilines and coupling with corresponding coupling components. Suitable diazo components are: 2-cyano-4-nitroaniline, 2,4-dicyanoaniline, 2,5-dicyanoaniline, 2,4-dicyano-6-chloroaniline, 2,4-dicyano-3,5-dimethylaniline, 2,5-dichloro-4-cyanoaniline, 2,4-dinitro-6-bromoaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-cyano-aniline, 2,6-dicyano-4-nitro-aniline, 2-cyano-4-nitro-6-methylsulphonylaniline, 2-cyano-4-nitro-6-chloro-aniline, 2-cyano-4-nitro-6-bromo-aniline, 4-carbamoylaniline and 4-sulphamoylaniline.
Suitable coupling components are: ##STR11##
The new dyestuffs can, however, also be obtained by, for example, reacting azo dyestuffs containing the grouping
--X--A--O--Z
wherein
X and A have the abovementioned meaning and
Z represents H with compounds of the formula
O═C═N--R.sub.4 (VIII)
or of the formula ##STR12## wherein
Q denotes chlorine or bromine and in the case that Z denotes phenoxycarbonyl, reacting with amines of the formula NHR1 R2 in a manner which is in itself known (compare, for example, GB Pat. No. 1,241,705).
Those dyestuffs which contain nitrile groups in the 2,6-position of the diazo component are advantageously obtained by reaction of corresponding 2,6-dihalogenoazo dyestuffs with CuCN or CuCN-forming substances in aprotic polar organic solvents at temperatures of about 60°-120° C in a known manner (compare GB-PS No. 1,125,683).
The new dyestuffs are particularly suitable for dyeing the abovementioned types of fibres from organic solvents by the exhaustion process, and for the continuous dyeing of, preferably, polyester fibres with aqueous and non-aqueous padding liquors.
100 parts of a polyethylene terephthalate fibre fabric are introduced into a dyebath which has been prepared from 1 part of the dyestuff of the formula ##STR13## which has been brought to a finely divided state by grinding, and 1,000 parts of tetrachloroethylene. The bath is brought to 120° C, with vigorous agitation of the liquor, and is kept at this temperature for 30 minutes. After brief cooling, the liquor is separated off and the dyed goods are rinsed three times with fresh perchloroethylene at 60° C. After drying, a strong intense red dyeing of high colour yield and very good fastness to light and to washing is obtained.
100 parts of a triacetate yarn are introduced into a dyebath which consists of 1 part of finely ground dyestuff of the formula ##STR14## and 1,000 parts of tetrachloroethylene. The dyebath is brought to 100° C with vigorous agitation of the liquor and is kept at this temperature for 30 minutes. After cooling, and rinsing the dyed goods with fresh tetrachloroethylene, a very strong red dyeing of good fastness to light and to washing is obtained.
100 parts of texturised polyethylene terephthalate fibres are introduced into a dyebath which has been prepared from 1 part of finely ground dyestuff of the formula ##STR15## 1,000 parts of tetrachloroethylene, 1 part of oleic acid ethanolamide, 1 part of oleyl alcohol eicosa-ethylene glycol ether and 6 parts of water.
The system is warmed to 120° C in a closed apparatus, with vigorous agitation of the liquor, and the fibres are dyed at this temperature for 30 minutes. After cooling to approx. 80° C and rinsing with fresh tetrachloroethylene at 60° C, a strong green dyeing of good colour yield and good fastness to light and washing is obtained.
100 parts of fibre yarn of poly-ε-caprolactam are introduced into a dyebath which contains 1 part of finely ground dyestuff of the formula ##STR16## and 1,000 parts of tetrachloroethylene.
The bath is brought to 100° C with vigorous agitation of the liquor and is kept at this temperature for 30 minutes. After separating off the dyeing liquor and twice rinsing with fresh tetrachloroethylene, a very deep and fast yellow dyeing is obtained.
If the procedure in Example IV is followed and the dyestuffs listed below are used, valuable dyeings, in the indicated colour shades, are again obtained:
__________________________________________________________________________
Colour shade:
__________________________________________________________________________
##STR17## yellow
##STR18## red
##STR19## bluish- tinged red
##STR20## red
##STR21## green
##STR22## orange
##STR23## scarlet
##STR24## brown
##STR25## violet
##STR26## violet
##STR27## red
##STR28## yellow
##STR29## orange
##STR30## golden yellow
##STR31## bluish- tinged red
##STR32## bluish- tinged red
##STR33## golden yellow
##STR34## golden yellow
##STR35## yellow
##STR36## golden yellow
##STR37## golden yellow
##STR38## yellow
##STR39## blue
##STR40## violet
##STR41## orange
##STR42## bluish- tinged red
##STR43## reddish- tinged orange
##STR44## orange
##STR45## orange
##STR46## orange
##STR47## yellow
##STR48## yellow
##STR49## blue
##STR50## claret
##STR51## blue
##STR52## orange
##STR53## orange
##STR54## bluish- tinged red
##STR55## violet
##STR56## blue
##STR57## blue
##STR58## orange
##STR59## yellow
##STR60## yellow
##STR61## yellow
##STR62## yellow
##STR63## bluish- tinged red
##STR64## bluish- tinged red
##STR65## blue
##STR66## blue
##STR67## violet
##STR68## blue
##STR69## orange
##STR70## red
##STR71## red
##STR72## red
##STR73## red
##STR74## yellow
##STR75## yellow
##STR76## orange
##STR77## blue
##STR78## bluish- tinged red
##STR79## orange
##STR80## bluish- tinged red
##STR81## violet
##STR82## violet
##STR83## blue
##STR84## red
##STR85## reddish- tinged blue
##STR86## blue
##STR87## blue
##STR88## ruby
##STR89## ruby
##STR90## reddish- tinged blue
##STR91## red
##STR92## violet
##STR93## violet
##STR94## claret
##STR95## red
##STR96## violet
##STR97## blue
##STR98## blue
##STR99## red-violet
##STR100## bluish- tinged red
##STR101## red
##STR102## bluish- tinged red
##STR103## bluish- tinged red
##STR104## red
##STR105## violet
##STR106## red
##STR107## yellow- brown
##STR108## yellow
##STR109## violet
##STR110## violet
##STR111## golden yellow
##STR112## ruby
##STR113## red
##STR114## yellow
__________________________________________________________________________
The abovementioned dyestuffs can be prepared in accordance with the following instructions:
163 g (1 mol) of 2-cyano-4-nitroaniline are introduced, whilst stirring and cooling to below 10° C, into a mixture of 900 g (500 cm3) of concentrated sulphuric acid (66° Be) and 170 cm3 of nitrosylsulphuric acid (100 cm3 contain 42 g of nitrite), and diazotised therein. Duration approx. 2 hours. The resulting clear diazo solution is then allowed to run into 500 cm3 of water, to which 4,000 g of ice are added gradually, the solution being introduced in such a way that the temperature remains below 5° C. The slight excess of nitrite is destroyed with amidosulphonic acid. A solution of 267 g (1 mol) of N,N-bis-(-β-carbamoylethyl)aniline in 1,000 cm3 of water and 195 g (170 cm3) of 30% strength hydrochloric acid is then allowed to run in. The coupling of the dyestuff is complete in approx. 1/2 hour. The mixture is stirred for a further 2 hours and the product is then filtered off and washed until neutral. After drying, the yield is 420 g.
35 g of the compound of the formula ##STR115## are dissolved in 100 g of anhydrous pyridine. 17 g of chloroformic acid phenyl ester are then slowly added at 0° C whilst stirring well, the mixture is stirred for a further two hours, excess ammonia gas is passed in, the whole is stirred at 40° for approx. 5 hours longer and is poured into water, and the pH is adjusted to 9-10 with NaOH. The dyestuff which precipitates is filtered off, washed until neutral and dried.
14.2 g of 2,4-dicyanoaniline are dissolved in 46 parts by weight of concentrated sulphuric acid to 0°-5° C and diazotised with 17.0 parts by weight of nitrosylsulphuric acid (42 g of nitrite in 100 cm3) whilst stirring well, and cooling; after about 3 hours the mixture is poured onto approx. 300 parts by weight of ice, a slight excess of nitrite is removed with amidosulphonic acid and the solution is filtered. This solution is then combined with a solution of 20.4 g of the compound of the formula ##STR116## in hydrochloric acid, the mixture is partially neutralised with dilute sodium hydroxide solution (using Congo Violet) and the coupling is completed by means of sodium acetate. The dyestuff is filtered off and washed. In the dry state, it is a dark red powder which dissolves in organic solvents, such as acetone or alcohol, to give a scarlet colour.
100 parts of a polyethylene terephthalate fibre fabric are introduced into a dyebath which has been prepared from 1 part of the dyestuff of the formula ##STR117## which has been brought to a finely divided state by grinding, and 1,000 parts of tetrachloroethylene. The bath is brought to 120° C whilst vigorously agitating the liquor and is kept at this temperature for 30 minutes. After brief cooling, the liquor is separated off and the dyed goods are rinsed three times with fresh perchloroethylene at 60° C. After drying, a strong intense scarlet dyeing of high colour yield and very good fastness to light and to washing is obtained.
100 parts of a triacetate yarn are introduced into a dyebath which consists of 1 part of finely ground dyestuff of the formula ##STR118## and 1,000 parts of tetrachloroethylene. The dyebath is brought to 100° C with vigorous agitation of the liquor and is kept at this temperature for 30 minutes. After cooling, and rinsing the dyed goods with fresh tetrachoroethylene, a very strong orange dyeing with good fastness to light and to washing is obtained.
100 parts of texturised polyethylene terephthalate fibres are introduced into a dyebath which has been prepared from 1 part of finely ground dyestuff of the formula ##STR119## 1,000 parts of tetrachloroethylene, 1 part of oleic acid ethanolamide, 1 part of oleyl alcohol eicosa-ethylene glycol ether and 6 parts of water.
The system is warmed to 120° C in a closed apparatus with vigorous agitation of the liquor, and the fibres are dyed at this temperature for 30 minutes. After cooling to approx. 80° C, and rinsing with fresh tetrachloroethylene at 60° C, a strong red dyeing of good colour yield and good fastness to light and to washing is obtained.
Comparably good results are obtained with the dyestuffs listed in the table which follows, which dye polyester fibres in the indicated colour shades.
__________________________________________________________________________
Colour shade
__________________________________________________________________________
##STR120## scarlet
##STR121## scarlet
##STR122## red
##STR123## orange
##STR124## red
##STR125## red
##STR126## bluish-tinged red
##STR127## bluish-tinged red
##STR128## bluish-tinged red
##STR129## bluish-tinged red
##STR130## bluish-tinged red
##STR131## ruby
##STR132## red-violet
##STR133## orange
##STR134## orange
##STR135## orange
##STR136## scarlet
##STR137## scarlet
##STR138## orange
##STR139## orange
##STR140## yellowish-tinged orange
##STR141## orange
##STR142## scarlet
##STR143## orange
##STR144## orange
##STR145## orange
##STR146## orange
##STR147## orange
##STR148## orange
##STR149## yellowish- tinged red
##STR150## yellowish- tinged red
##STR151## orange
__________________________________________________________________________
100 parts of the dyestuff of the formula indicated in Example VIII, 40 parts of the reaction product of 1 mol of 2'-benzyl-4-hydroxy-diphenyl with 12 mols of ethylene oxide and 470 parts of water are ground together in a ball mill. 98 parts of the stable, finely disperse dyestuff paste thus obtained (dyestuff content: 16.4%) are diluted to 1 1 with water. A polyethylene terephthalate fabric is padded with this dyestuff liquor; after squeezing out to a weight increase of 100%, drying at 80° C and thermosol treatment for 60 seconds at 190° C, the fabric is washed in tetrachloroethylene at room temperature and is then dried.
A scarlet dyeing of excellent rub resistance is obtained, with a high fixing yield.
100 parts of the dyestuff of the formula indicated in Example IX, 50 parts of the reaction product of 1 mol of pnonylphenol and 30 mols of ethylene oxide, and 480 parts of water are ground together. 98 parts of the stable, finely disperse paste (dyestuff content: 15.9%) are diluted to 1 1 with water. A knitted polyethylene terephthalate fabric is impregnated with this dyeing liquor; after squeezing out to a weight increase of 100%, drying at 90° C and a dry heat treatment of 60 seconds at 200° C, the knitted fabric is washed with tetrachloroethylene at room temperature.
An even, brilliant orange dyeing of excellent rub resistance is obtained, with a high fixing yield.
Claims (8)
1. In a process for dyeing a synthetic fibre material from an organic water-immiscible solvent by the exhaustion process, the improvement comprising employing a dispersion of a dyestuff of the formula: ##STR152## wherein D is the radical of an aromatic carbocyclic or aromatic-heterocyclic diazo component;
Q1 is hydrogen; C1 -C4 -alkyl; C1 -C4 alkoxy; halogen; C2 -C5 alkylcarbonylamino which is unsubstituted or substituted with hydroxyl, halogen, CN, or C1 -C4 -alkoxy; phenylcarbonylamino which is unsubstituted or mono-, di, or tri-substituted with C1 -C4 -alkyl; C1 -C4 -alkoxy, halogen, hydroxyl, formylamino, or ureido;
Q2 is hydrogen, C1 -C4 -alkyl, C1 -C4 -alkoxy or halogen;
Q3 is hydrogen, C2 H4 OCONHQ4, C1 -C4 -alkyl which is unsubstituted or substituted with CN, Cl, -CONH2 or C1 -C2 -alkoxy;
Q4 is hydrogen, amino, C1 -C4 -hydroxyalkylamino, OH, methyl, or hydroxphenyl; and
A' is C1 -C4 -alkylene; in the dyeing liquor.
2. The process of claim 1 wherein A' is --C2 H4 --.
3. The process of claim 1 wherein Q4 is hydrogen.
4. The process of claim 1 wherein D is a radical of the formula ##STR153## T1 is H, NO2, CN, halogen, or --CONH2 ; T2 is H, NO2, CN, CONH2 or SO2 NH2 ;
T3 is H, NO2, CN, halogen, or C1 -C4 -alkylsulfonyl; and
T4 is H or halogen.
5. The process of claim 4 wherein Q1 is formylamino.
6. In a process for dyeing a synthetic fibre material from an organic water-immiscible solvent by the exhaustion process, the improvement comprising employing a dispersion of a dyestuff of the formula:
Y.sub.1 --Ar--N═N--B--Y.sub.2
wherein
Ar is unsubstituted or substituted benzene free of ionic groups;
B is unsubstituted or substituted pyrazolone, aminopyrazole, indole, or imidazole; and
Y1 and Y2 independently of one another are hydrogen or --X--A--OCONR1 R2, wherein X is a direct bond or a bridging group, A is alkylene, R1 is hydrogen or alkyl, and R2 is hydrogen, alkyl, cycloalkyl, aralkyl, aryl or substituted or unsubstituted amino, with the proviso that Y1 and Y2 are not simultaneously hydrogen; in the dyeing liquor.
7. Process of claim 6 wherein R1 and R2 are hydrogen.
8. The process of claim 1 wherein said dyeing liquor further includes a non-ionic auxiliary or mixtures thereof in the amount of from about 0.05% to about 2% by weight of said organic solvent.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732328160 DE2328160C3 (en) | 1973-06-02 | Exhaust process for dyeing synthetic fiber materials | |
| DT2328160 | 1973-06-02 | ||
| DE2411290A DE2411290A1 (en) | 1974-03-09 | 1974-03-09 | Exhaust dyeing synthetic fibres from dispersion - of carbamate gp contg azo dye in water-immiscible org solvent, giving good build-up and general fastness |
| US47499074A | 1974-05-31 | 1974-05-31 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US47499074A Continuation | 1973-06-02 | 1974-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4083685A true US4083685A (en) | 1978-04-11 |
Family
ID=27185309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/703,013 Expired - Lifetime US4083685A (en) | 1973-06-02 | 1976-07-06 | Process for dyeing synthetic fibre materials from an organic water-immiscible solvent |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US4083685A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030208088A1 (en) * | 2001-09-06 | 2003-11-06 | Rajnish Batlaw | Novel intermediates for the production of ink system colorants |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2238486A (en) * | 1939-11-13 | 1941-04-15 | Eastman Kodak Co | Azo compounds and material colored therewith |
| US3069408A (en) * | 1956-07-18 | 1962-12-18 | Sandoz Ltd | Water-insoluble azo dyestuffs |
| FR1360450A (en) | 1963-05-07 | 1964-05-08 | Bayer Ag | Water insoluble azo dyes and process for their preparation |
| GB1237017A (en) | 1969-02-28 | 1971-06-30 | Yorkshire Dyeware & Chem Co | Improvements in and relating to azo dyes |
| US3740189A (en) * | 1970-09-17 | 1973-06-19 | Gaf Corp | Black dye formulation containing three mono-azo dyes |
| US3773750A (en) * | 1970-02-02 | 1973-11-20 | Sandoz Ltd | 2,6-dihalo-4-nitrophenyl-azo-phenylcompounds having an optionally substituted phenylcarbamoyloxyalkyl substituent |
| US3792971A (en) * | 1969-10-18 | 1974-02-19 | Bayer Ag | Exhaust process for the dyeing of synthetic fibre materials |
| GB1468908A (en) | 1973-05-18 | 1977-03-30 | Hoechst Ag | Process for the exhaust dyeing of synthetic fibres from organic solvents |
-
1976
- 1976-07-06 US US05/703,013 patent/US4083685A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2238486A (en) * | 1939-11-13 | 1941-04-15 | Eastman Kodak Co | Azo compounds and material colored therewith |
| US3069408A (en) * | 1956-07-18 | 1962-12-18 | Sandoz Ltd | Water-insoluble azo dyestuffs |
| FR1360450A (en) | 1963-05-07 | 1964-05-08 | Bayer Ag | Water insoluble azo dyes and process for their preparation |
| GB1237017A (en) | 1969-02-28 | 1971-06-30 | Yorkshire Dyeware & Chem Co | Improvements in and relating to azo dyes |
| US3792971A (en) * | 1969-10-18 | 1974-02-19 | Bayer Ag | Exhaust process for the dyeing of synthetic fibre materials |
| US3773750A (en) * | 1970-02-02 | 1973-11-20 | Sandoz Ltd | 2,6-dihalo-4-nitrophenyl-azo-phenylcompounds having an optionally substituted phenylcarbamoyloxyalkyl substituent |
| US3740189A (en) * | 1970-09-17 | 1973-06-19 | Gaf Corp | Black dye formulation containing three mono-azo dyes |
| GB1468908A (en) | 1973-05-18 | 1977-03-30 | Hoechst Ag | Process for the exhaust dyeing of synthetic fibres from organic solvents |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030208088A1 (en) * | 2001-09-06 | 2003-11-06 | Rajnish Batlaw | Novel intermediates for the production of ink system colorants |
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